US6102986A - Method of inhibiting gas hydrate formation - Google Patents

Method of inhibiting gas hydrate formation Download PDF

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Publication number
US6102986A
US6102986A US09/230,156 US23015699A US6102986A US 6102986 A US6102986 A US 6102986A US 23015699 A US23015699 A US 23015699A US 6102986 A US6102986 A US 6102986A
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groups
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gas
amine oxide
addition
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Peter Klug
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Clariant Produkte Deutschland GmbH
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Clariant GmbH
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/52—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning

Definitions

  • Gas hydrates are crystalline inclusion compounds of gas molecules in water, which form under certain temperature and pressure conditions (low temperature and high pressure). In the process, the water molecules form cage structures around the gas molecules in question.
  • the lattice framework formed solely from water molecules is thermodynamically unstable, the lattice only being stabilized by the inclusion of gas molecules with the formation of an ice-like compound which, depending on the pressure and the gas composition, may exist even beyond the freezing point of water (up to above 25° C.).
  • gas hydrate formation may also present problems during drilling to develop new gas or petroleum reservoirs.
  • thermodynamic inhibition the addition of these thermodynamic inhibitors does, however, cause major safety problems (flash point and toxicity of the alcohols), logistics problems (large storage tanks, recycling of these solvents) and correspondingly high cost, especially in offshore production.
  • thermodynamic inhibitors by the addition, in the temperature and pressure ranges within which gas hydrates are able to form, of additives (amount used ⁇ 2%) which either delay gas hydrate formation (threshold hydrate inhibitors, kinetic inhibition) or cause gas hydrate agglomerates to be small and pumpable, so that they can be transported through a pipeline (so-called agglomerate inhibitors or anti-agglomerates).
  • gas hydrate inhibitors described in the patent literature include not only the known thermodynamic inhibitors, but also a multiplicity of both monomeric and polymeric classes of substances which represent kinetic or agglomerate inhibitors.
  • Patent Application WO 95/17579 describes quaternary ammonium compounds, especially those which carry butyl or pentyl groups on the quaternary center, as gas hydrate inhibitors. Mixtures of such quaternary ammonium salts with corrosion inhibitors and amidic polymers are mentioned in WO 96/04462.
  • WO 96/08636 describes surface-active substances as gas hydrate inhibitors which carry a polar head group and a hydrophobic radical, the hydrophobic radical containing no more than 12 carbon atoms.
  • thermodynamic inhibitors methanol and glycols
  • amine oxides or their salts are particularly suitable as gas hydrate inhibitors. As shown in the appended Examples, they are capable, when added in small amounts, of effective suppression of the formation of gas hydrates. Furthermore, the especially effective amine oxides exhibit virtually no surfactant activity, which is particularly beneficial in terms of their foaming behavior, since standard surfactant additives often cause grave foaming problems.
  • the invention therefore relates to a method for inhibiting gas hydrate formation, which comprises the addition to the aqueous phase, in the case of multiphase mixtures (of gas, water and possibly condensate), of an amine oxide or salts thereof.
  • the method according to the invention preferably employs amine oxides of the formula
  • R 1 , R 2 and R 3 independently of one another, are C 1 -C 30 -alkyl, C 2 -C 30 -alkenyl, C 7 -C 30 -alkylaryl, C 7 -C 30 -arylalkyl or C 6 -C 10 -aryl, where the alkyl and alkenyl groups may be interrupted by --O--, --NHCO-- or --O--CO-- and may be substituted by hydroxyl groups, carbonyl groups, carbonamide groups or alkoxycarboxyl groups and two or three groups R 1 , R 2 and R 3 , together with the nitrogen atom to which they are bound may form a mono- or bicyclic ring having from 4 to 10 carbon atoms, where one such monocyclic ring may contain an oxygen atom instead of a --CH 2 -- unit.
  • R 1 , R 2 and R 3 independently of one another, are C 1 -C 8 -alkyl or C 2 -C 8 -alkenyl which may be interrupted by oxygen atoms and may be substituted by hydroxyl groups, carboxyl groups, carbonamide groups or alkoxycarbonyl groups and two groups R 1 , R 2 and R 3 may form a morpholine ring.
  • X is the anion of a mineral acid, carboxylic acid or sulfonic acid.
  • examples of such anions are halide, sulfate, phosphate, nitrate and the anions of C 1 -C 12 -alkanoic acids such as formate, acetate, propionate, butyrate and isobutyrate, n-pentanoate, methylbutyrate, pivalate, octanoate and laurate.
  • the synthesis of the amine oxides is carried out according to methods known per se, preferentially by oxidation of the corresponding tertiary amine with peroxides or peracids, preferably by oxidation with hydrogen peroxide in aqueous or aqueous/alcoholic solution as shown e.g. in J. Am. Chem. Soc. 1957, 79, 964. Under these conditions a low-viscosity solution of the desired amine oxides in water or alcohol/water mixtures is produced directly.
  • the products may also be employed as an anhydrous pure substance, but advantageously they are generally used in the form of an aqueous solution, to ensure convenient proportioning at low viscosity.
  • the amine oxides are added to the multiphase mixture of gas and water by means of standard equipment such as injection pumps or the like, the good water solubility of the amine oxides resulting in rapid and uniform distribution of the inhibitor in the aqueous phase which has a tendency to form hydrates. It is generally sufficient for the aqueous amine oxide solution to be added to ensure uniform distribution.
  • the addition of the inhibitor must take place before gas hydrates are formed, i.e. still above the equilibrium temperature of hydrate formation. That is generally the case if the inhibitor is added directly at the natural gas source.
  • the amine oxides can be employed on their own or in combination with other known gas hydrate inhibitors.
  • the amount of the novel gas hydrate inhibitors used will be sufficient to achieve adequate inhibition.
  • Typical use concentrations, calculated as 100% of active substance, are from 0.01 to 2 wt %, especially concentrations of from 0.02 to 1 wt % (100-10,000 ppm), based on the aqueous phase.
  • polymers having a carbon backbone obtained by polymerization, and amide bonds in the side chains include, in particular, polymers such as poly(vinylpyrrolidone), poly(vinylcaprolactam), copolymers from vinylpyrrolidone and vinylcaprolactam, and terpolymers of vinylpyrrolidone, vinylcaprolactam and further anionic, cationic and neutral comonomers having a vinylic double bond such as 1-olefin, N-alkylacrylamides, N-vinylacetamide, acrylamide, sodium 2-acrylamido-2-methyl-1-propanesulfonate (AMPS) or acrylic acid.
  • polymers such as poly(vinylpyrrolidone), poly(vinylcaprolactam), copolymers from vinylpyrrolidone and vinylcaprolactam, and terpolymers of vinylpyrrolidone, vinylcaprolactam and further anionic, cationic and neutral comonomers having a vinylic double bond such as
  • N,N-dialkylacrylamides such as N-acryloylpyrrolidone, N-acryloylmorpholine and N-acryloylpiperidine.
  • Likwise suitable are mixtures with alkylpolyglycosides, hydroxylethycellulose, carboxymethylcellulose and other ionic or nonionic surfactant molecules.
  • THF hydrate formation commences rapidly without an inhibitor (Example 1) under the experimental conditions and leads to the formation of THF hydrates in the form of needles or flakes which very rapidly cause the entire test solution to solidify.
  • the addition of an amine oxide or amine oxide salt (Examples 2-13) considerably slows down THF hydrate formation and/or modifies the crystal form of the hydrates produced.
  • the THF test was carried out as follows:
  • the frozen pipette is taken from the refrigerator, quickly wiped (to remove crystal nuclei on the outside of the pipette and thus obtain uniform starting conditions) and immediately immersed to a depth of about 15 mm into the above THF/water/sodium chloride mixture, THF hydrates forming after a short time (a few minutes).
  • the pipette is very carefully withdrawn from the test tube and the pipette with the cork stopper and adhering hydrates is immediately tared. Based on the difference between the original weight and the weight at this point and on the time elapsed, the growth rate of THF hydrate formation is calculated (in g/h).
  • Example 2 The same procedure is followed as in Example 1, except that the test solution has 5000 ppm of the corresponding inhibitor added to it.
  • the crystal growth time is increased from 5 min to, if necessary, 1 h if no rapid hydrate growth is observed.
  • the evaluation is carried out as above. The crystal form of the hydrates formed is noted.
  • amine oxides were prepared in accordance with the following general procedure: 0.50 mol of the corresponding tertiary amine was dissolved in 150 ml of isopropanol, and 1.50 mol of 35% strength aqueous hydrogen peroxide were added dropwise within 30 min.
  • water-insoluble amines tributylamine, tripentylamine
  • the reaction mixture then consists of two phases. This was followed by vigorous stirring at 25° C. for about 2-30 h (depending on the water solubility of the amine), a single-phase clear solution of the amine oxide in water being formed which, after the reaction was complete, no longer produced a purple color with phenolphthalein.
  • the mixture was heated for 2 h to 60-80° C. This resulted in an aqueous isopropanolic solution of the corresponding amine oxide.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US09/230,156 1996-07-23 1997-07-17 Method of inhibiting gas hydrate formation Expired - Fee Related US6102986A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19629662 1996-07-23
DE19629662A DE19629662A1 (de) 1996-07-23 1996-07-23 Verfahren zur Inhibierung der Gashydratbildung
PCT/EP1997/003831 WO1998003615A1 (de) 1996-07-23 1997-07-17 Verfahren zur inhibierung der gashydratbildung

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Country Status (8)

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US (1) US6102986A (de)
EP (1) EP0914407B1 (de)
AU (1) AU3695397A (de)
CA (1) CA2261982C (de)
DE (2) DE19629662A1 (de)
ID (1) ID17556A (de)
NO (1) NO317756B1 (de)
WO (1) WO1998003615A1 (de)

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6596911B2 (en) * 2000-02-22 2003-07-22 Baker Hughes Incorporation Composition and method for inhibition of formation of gas hydrates
US20040110998A1 (en) * 2002-09-03 2004-06-10 Rivers Gordon T. Gas hydrate inhibitors
US20040164278A1 (en) * 2003-02-24 2004-08-26 Clariant Gmbh Corrosion and gas hydrate inhibitors having improved water solubility and increased biodegradability
US20040163306A1 (en) * 2003-02-24 2004-08-26 Clariant Gmbh Additives for inhibiting gas hydrate formation
US20040167040A1 (en) * 2003-02-24 2004-08-26 Clariant Gmbh Corrosion and gas hydrate inhibitors having improved water solubility and increased biodegradability
US6867262B1 (en) * 1999-07-28 2005-03-15 Basf Aktiengesellschaft Grafted polymers as gas hydrate inhibitors
US20050085676A1 (en) * 2003-10-21 2005-04-21 Vaithilingam Panchalingam Methods for inhibiting hydrate blockage in oil and gas pipelines using betaines and amine oxides
US20050101495A1 (en) * 2003-02-24 2005-05-12 Clariant Gmbh Corrosion and gas hydrate inhibitors having improved water solubility and increased biodegradability
US20060205603A1 (en) * 2003-07-02 2006-09-14 Colle Karla S Method for inhibiting hydrate formation
US20060237691A1 (en) * 2005-04-26 2006-10-26 Meier Ingrid K Amine-based gas hydrate inhibitors
US7323609B2 (en) 2003-02-24 2008-01-29 Clariant Produkte (Deutschland) Gmbh Corrosion and gas hydrate inhibitors having improved water solubility and increased biodegradability
US20090078406A1 (en) * 2006-03-15 2009-03-26 Talley Larry D Method of Generating a Non-Plugging Hydrate Slurry
US20090221451A1 (en) * 2006-03-24 2009-09-03 Talley Larry D Composition and Method for Producing a Pumpable Hydrocarbon Hydrate Slurry at High Water-Cut
US7615102B2 (en) 2004-10-07 2009-11-10 Clariant Produkte (Deutschland) Gmbh Corrosion and gas hydrate inhibitors with an increased biological degradability and a reduced toxicity
US20100113845A1 (en) * 2008-11-05 2010-05-06 Osegovic John P Accelerated hydrate formation and dissociation
WO2013053770A1 (en) 2011-10-11 2013-04-18 Eco Inhibitors As Method of inhibiting the formation of gas hydrates using amine oxides
US8430169B2 (en) 2007-09-25 2013-04-30 Exxonmobil Upstream Research Company Method for managing hydrates in subsea production line
KR101360738B1 (ko) 2012-06-22 2014-02-11 한국교통대학교산학협력단 가스 하이드레이트 생성 촉진제 및 가스 하이드레이트 생성 촉진 방법
US8920542B2 (en) 2009-06-25 2014-12-30 Clariant Finance (Bvi) Limited Additives for inhibiting gas hydrate formation
WO2016170473A1 (en) * 2015-04-23 2016-10-27 Chimec S.P.A. A composition comprising an amine oxide and a tenside and use thereof in petroleum field
US9988568B2 (en) 2015-01-30 2018-06-05 Ecolab Usa Inc. Use of anti-agglomerants in high gas to oil ratio formations
WO2020161407A1 (fr) 2019-02-06 2020-08-13 Arkema France Composition pour prévenir l'agglomération d'hydrates de gaz

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2543426C (en) * 2003-10-21 2010-12-07 Champion Technologies, Inc. Methods for inhibiting hydrate blockage in oil and gas pipelines using simple quaternary ammonium and phosphonium compounds
US8993488B2 (en) 2011-02-24 2015-03-31 United Laboratories International, Llc Process for removal of hydrogen sulfide in downhole oilfield applications

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3213593A (en) * 1963-07-08 1965-10-26 Richfield Oil Corp Reduction of hydrate formation in gas production equipment
FR2618876A1 (fr) * 1987-07-30 1989-02-03 Inst Francais Du Petrole Procede de traitement et de transport d'un gaz contenant du methane et de l'eau
US4973775A (en) * 1987-12-30 1990-11-27 Institut Francais Du Petrole Process for delaying the formation and/or reducing the agglomeration tendency of hydrates
US5600044A (en) * 1994-09-15 1997-02-04 Exxon Production Research Company Method for inhibiting hydrate formation
US5744665A (en) * 1995-06-08 1998-04-28 Exxon Production Research Company Maleimide copolymers and method for inhibiting hydrate formation
US5789635A (en) * 1996-02-07 1998-08-04 Institut Francais Du Petrole Method for inhibiting or retarding hydrate formation, growth and/or agglomeration
US5817898A (en) * 1995-04-26 1998-10-06 Institut Francais Du Petrole Process for inhibiting or retarding the formation, growth and/or aggregation of hydrates in production effluents
US5841010A (en) * 1994-09-15 1998-11-24 Exxon Production Research Company Surface active agents as gas hydrate inhibitors
US5874660A (en) * 1995-10-04 1999-02-23 Exxon Production Research Company Method for inhibiting hydrate formation
US5981816A (en) * 1996-05-15 1999-11-09 Institut Francais Du Petrole Method for inhibiting or retarding hydrate formation or agglomeration in a production effluent

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK0770169T3 (da) * 1994-08-05 2000-01-03 Bp Exploration Operating Hydratinhibering

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3213593A (en) * 1963-07-08 1965-10-26 Richfield Oil Corp Reduction of hydrate formation in gas production equipment
FR2618876A1 (fr) * 1987-07-30 1989-02-03 Inst Francais Du Petrole Procede de traitement et de transport d'un gaz contenant du methane et de l'eau
US4973775A (en) * 1987-12-30 1990-11-27 Institut Francais Du Petrole Process for delaying the formation and/or reducing the agglomeration tendency of hydrates
US5600044A (en) * 1994-09-15 1997-02-04 Exxon Production Research Company Method for inhibiting hydrate formation
US5841010A (en) * 1994-09-15 1998-11-24 Exxon Production Research Company Surface active agents as gas hydrate inhibitors
US5817898A (en) * 1995-04-26 1998-10-06 Institut Francais Du Petrole Process for inhibiting or retarding the formation, growth and/or aggregation of hydrates in production effluents
US5744665A (en) * 1995-06-08 1998-04-28 Exxon Production Research Company Maleimide copolymers and method for inhibiting hydrate formation
US5874660A (en) * 1995-10-04 1999-02-23 Exxon Production Research Company Method for inhibiting hydrate formation
US5789635A (en) * 1996-02-07 1998-08-04 Institut Francais Du Petrole Method for inhibiting or retarding hydrate formation, growth and/or agglomeration
US5981816A (en) * 1996-05-15 1999-11-09 Institut Francais Du Petrole Method for inhibiting or retarding hydrate formation or agglomeration in a production effluent

Cited By (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6867262B1 (en) * 1999-07-28 2005-03-15 Basf Aktiengesellschaft Grafted polymers as gas hydrate inhibitors
US6596911B2 (en) * 2000-02-22 2003-07-22 Baker Hughes Incorporation Composition and method for inhibition of formation of gas hydrates
AU2001239852B2 (en) * 2000-02-22 2005-10-20 Baker Hughes Incorporated Composition and method for inhibition of formation of gas hydrates
US20040110998A1 (en) * 2002-09-03 2004-06-10 Rivers Gordon T. Gas hydrate inhibitors
US7837746B2 (en) 2002-09-03 2010-11-23 Baker Hughes Incorporated Gas hydrate inhibitors
US20070032689A1 (en) * 2002-09-03 2007-02-08 Baker Hughes Incorporated Gas hydrate inhibitors
US7164051B2 (en) 2002-09-03 2007-01-16 Baker Hughes Incorporated Gas hydrate inhibitors
US20050101495A1 (en) * 2003-02-24 2005-05-12 Clariant Gmbh Corrosion and gas hydrate inhibitors having improved water solubility and increased biodegradability
US7341617B2 (en) 2003-02-24 2008-03-11 Clariant Produkte (Deutschland) Gmbh Corrosion and gas hydrate inhibitors having improved water solubility and increased biodegradability
US7435845B2 (en) 2003-02-24 2008-10-14 Clariant Produkte (Deutschland) Gmbh Corrosion and gas hydrate inhibitors having improved water solubility and increased biodegradability
US7348451B2 (en) 2003-02-24 2008-03-25 Clariant Produkte (Deutschland) Gmbh Additives for inhibiting gas hydrate formation
US7323609B2 (en) 2003-02-24 2008-01-29 Clariant Produkte (Deutschland) Gmbh Corrosion and gas hydrate inhibitors having improved water solubility and increased biodegradability
US7253138B2 (en) 2003-02-24 2007-08-07 Clariant Produkte (Deutschland) Gmbh Corrosion and gas hydrate inhibitors having improved water solubility and increased biodegradability
US20070173672A1 (en) * 2003-02-24 2007-07-26 Clariant Gmbh Additives for inhibiting gas hydrate formation
US20040164278A1 (en) * 2003-02-24 2004-08-26 Clariant Gmbh Corrosion and gas hydrate inhibitors having improved water solubility and increased biodegradability
US20040167040A1 (en) * 2003-02-24 2004-08-26 Clariant Gmbh Corrosion and gas hydrate inhibitors having improved water solubility and increased biodegradability
US20040163306A1 (en) * 2003-02-24 2004-08-26 Clariant Gmbh Additives for inhibiting gas hydrate formation
US7214814B2 (en) 2003-02-24 2007-05-08 Clariant Produkte (Deutschland) Gmbh Additives for inhibiting gas hydrate formation
US20060205603A1 (en) * 2003-07-02 2006-09-14 Colle Karla S Method for inhibiting hydrate formation
US7585816B2 (en) 2003-07-02 2009-09-08 Exxonmobil Upstream Research Company Method for inhibiting hydrate formation
US20050081432A1 (en) * 2003-10-21 2005-04-21 Vaithilingam Panchalingam Methods for inhibiting hydrate blockage in oil and gas pipelines using amide compounds
US20050085676A1 (en) * 2003-10-21 2005-04-21 Vaithilingam Panchalingam Methods for inhibiting hydrate blockage in oil and gas pipelines using betaines and amine oxides
US7264653B2 (en) 2003-10-21 2007-09-04 Champion Technologies, Inc. Methods for inhibiting hydrate blockage in oil and gas pipelines using simple quaternary ammonium and phosphonium compounds
US20050085396A1 (en) * 2003-10-21 2005-04-21 Vaithilingam Panchalingam Methods for inhibiting hydrate blockage in oil and gas pipelines using amino alcohols and ester compounds
US20050081714A1 (en) * 2003-10-21 2005-04-21 Vaithilingam Panchalingam Methods for inhibiting hydrate blockage in oil and gas pipelines using simple quaternary ammonium and phosphonium compounds
US7381689B2 (en) 2003-10-21 2008-06-03 Champion Technologies, Inc. Methods for inhibiting hydrate blockage in oil and gas pipelines using amide compounds
US20050085675A1 (en) * 2003-10-21 2005-04-21 Vaithilingam Panchalingam Methods for inhibiting hydrate blockage in oil and gas pipelines using ester compounds
US7615102B2 (en) 2004-10-07 2009-11-10 Clariant Produkte (Deutschland) Gmbh Corrosion and gas hydrate inhibitors with an increased biological degradability and a reduced toxicity
EP1717288A3 (de) * 2005-04-26 2007-03-21 Air Products and Chemicals, Inc. Aminbasierende Gashydratinhibitoren
US7452848B2 (en) 2005-04-26 2008-11-18 Air Products And Chemicals, Inc. Amine-based gas hydrate inhibitors
US20060237691A1 (en) * 2005-04-26 2006-10-26 Meier Ingrid K Amine-based gas hydrate inhibitors
US20090078406A1 (en) * 2006-03-15 2009-03-26 Talley Larry D Method of Generating a Non-Plugging Hydrate Slurry
US8436219B2 (en) 2006-03-15 2013-05-07 Exxonmobil Upstream Research Company Method of generating a non-plugging hydrate slurry
US20090221451A1 (en) * 2006-03-24 2009-09-03 Talley Larry D Composition and Method for Producing a Pumpable Hydrocarbon Hydrate Slurry at High Water-Cut
US7958939B2 (en) 2006-03-24 2011-06-14 Exxonmobil Upstream Research Co. Composition and method for producing a pumpable hydrocarbon hydrate slurry at high water-cut
US8430169B2 (en) 2007-09-25 2013-04-30 Exxonmobil Upstream Research Company Method for managing hydrates in subsea production line
US8334418B2 (en) * 2008-11-05 2012-12-18 Water Generating Systems LLC Accelerated hydrate formation and dissociation
US20100113845A1 (en) * 2008-11-05 2010-05-06 Osegovic John P Accelerated hydrate formation and dissociation
US8920542B2 (en) 2009-06-25 2014-12-30 Clariant Finance (Bvi) Limited Additives for inhibiting gas hydrate formation
WO2013053770A1 (en) 2011-10-11 2013-04-18 Eco Inhibitors As Method of inhibiting the formation of gas hydrates using amine oxides
KR101360738B1 (ko) 2012-06-22 2014-02-11 한국교통대학교산학협력단 가스 하이드레이트 생성 촉진제 및 가스 하이드레이트 생성 촉진 방법
US9988568B2 (en) 2015-01-30 2018-06-05 Ecolab Usa Inc. Use of anti-agglomerants in high gas to oil ratio formations
WO2016170473A1 (en) * 2015-04-23 2016-10-27 Chimec S.P.A. A composition comprising an amine oxide and a tenside and use thereof in petroleum field
EA034982B1 (ru) * 2015-04-23 2020-04-14 Кимек С.П.А. Композиция, содержащая аминоксид и тензид, и ее применение в нефтяной отрасли
WO2020161407A1 (fr) 2019-02-06 2020-08-13 Arkema France Composition pour prévenir l'agglomération d'hydrates de gaz

Also Published As

Publication number Publication date
EP0914407B1 (de) 2000-01-05
NO990140L (no) 1999-01-13
DE19629662A1 (de) 1998-01-29
CA2261982C (en) 2006-10-31
NO317756B1 (no) 2004-12-13
DE59700988D1 (de) 2000-02-10
NO990140D0 (no) 1999-01-13
CA2261982A1 (en) 1998-01-29
WO1998003615A1 (de) 1998-01-29
EP0914407A1 (de) 1999-05-12
AU3695397A (en) 1998-02-10
ID17556A (id) 1998-01-08

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